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香豆素

香豆素 基本信息

香豆素(Coumarin)是一类具有独特芳香气味的化合物,化学式为C9H6O2。它们属于苯骈α-呋喃酮类化合物,在自然界中广泛存在。

结构特征

香豆素的基本结构由苯环和呋喃酮构成,其中苯环与四个碳原子相连的呋喃酮单元形成独特的“香豆素环”。

自然来源

香豆素存在于多种植物、真菌及动物体内。在植物界中,它主要作为天然防御机制的一部分,用作对昆虫的化学信号。著名的例子包括:天竺葵科(如紫花苜蓿)、唇形科(如薄荷)和芸香科(如柑橘属果实)。此外,在真菌、苔藓及藻类中也有发现。

化学性质 稳定性

由于其独特的结构,香豆素表现出良好的化学稳定性。它们不易被氧化或还原,但可以与其他化合物发生多种类型的反应,包括缩合、取代等。

生物活性

许多香豆素衍生物具有生物活性,能够引起抗菌、抗炎、抗氧化等多种作用。这些特性使它们成为医药、食品添加剂等多个领域的重要研究对象。

应用领域 医药行业

在制药业中,某些结构类似物被开发为药物先导化合物。例如,香豆素类抗生素是最早的广谱抗生素之一;一些香豆素衍生物还表现出抗癌潜力。

食品工业

由于其独特的香气和味道,在食品加工中也得到了广泛应用,常作为香精成分使用。

其他应用

此外,它们还在染料生产、农药开发等多个领域展现出潜在价值。

生产方法

香豆素可通过多种合成路径获得。传统的化学合成涉及从苯甲醛出发的反应;而近年来,通过生物转化技术,利用微生物发酵过程制备天然香豆素也成为一种可持续的方法。

总之,香豆素因其独特的结构和广泛的生物学应用,在多个领域中发挥着重要作用,并且仍然是有机化学研究中的一个重要课题。

中文名称 英文名称 CAS号 化学式 结构式图片
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)isoxazole-4-sulfonamide —— C14H16N2O4S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)isoxazole-4-sulfonamide
—— 1-(4-chlorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)methanesulfonamide —— C18H20ClNO3S
1-(4-chlorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)methanesulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide —— C23H27NO4
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)oxy)acetamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(3-fluorophenyl)methanesulfonamide —— C18H20FNO3S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(3-fluorophenyl)methanesulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-3-phenylpropanamide —— C20H23NO2
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-3-phenylpropanamide
—— 1-(1-(2,3-Dihydrobenzofuran-5-yl)propan-2-yl)-3-ethylurea —— C14H20N2O2
1-(1-(2,3-Dihydrobenzofuran-5-yl)propan-2-yl)-3-ethylurea
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)acetamide 1904045-04-0 C13H17NO2
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)acetamide
—— 3-(2-chlorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-5-methylisoxazole-4-carboxamide —— C22H21ClN2O3
3-(2-chlorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-5-methylisoxazole-4-carboxamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-ethoxyacetamide —— C15H21NO3
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-ethoxyacetamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-5-methylthiophene-2-sulfonamide —— C16H19NO3S2
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-5-methylthiophene-2-sulfonamide
—— 1-(1-(2,3-Dihydrobenzofuran-5-yl)propan-2-yl)-3-phenethylurea —— C20H24N2O2
1-(1-(2,3-Dihydrobenzofuran-5-yl)propan-2-yl)-3-phenethylurea
—— (E)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-phenylethenesulfonamide —— C19H21NO3S
(E)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-phenylethenesulfonamide
—— (3r,5r,7r)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)adamantane-1-carboxamide —— C22H29NO2
(3r,5r,7r)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)adamantane-1-carboxamide
—— 3-(3-chlorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)propanamide —— C20H22ClNO2
3-(3-chlorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)propanamide
—— 1-(2,5-difluorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)methanesulfonamide —— C18H19F2NO3S
1-(2,5-difluorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)methanesulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(thiophen-2-yl)cyclopropanecarboxamide —— C19H21NO2S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(thiophen-2-yl)cyclopropanecarboxamide
—— 2-cyclohexyl-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)acetamide —— C19H27NO2
2-cyclohexyl-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)acetamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-(4-methoxyphenyl)ethanesulfonamide —— C20H25NO4S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-(4-methoxyphenyl)ethanesulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)pent-4-enamide —— C16H21NO2
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)pent-4-enamide
—— 1-Allyl-3-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)urea —— C15H20N2O2
1-Allyl-3-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)urea
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-5-ethylthiophene-2-sulfonamide —— C17H21NO3S2
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-5-ethylthiophene-2-sulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-4-methylthiophene-2-carboxamide —— C17H19NO2S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-4-methylthiophene-2-carboxamide
—— 1-Cyclopentyl-3-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)urea —— C17H24N2O2
1-Cyclopentyl-3-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)urea
—— 5-chloro-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)thiophene-2-sulfonamide —— C15H16ClNO3S2
5-chloro-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)thiophene-2-sulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-(m-tolyloxy)acetamide —— C20H23NO3
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-(m-tolyloxy)acetamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-phenylethanesulfonamide —— C19H23NO3S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-phenylethanesulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)cyclopropanesulfonamide —— C14H19NO3S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)cyclopropanesulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-5-nitrofuran-2-carboxamide —— C16H16N2O5
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-5-nitrofuran-2-carboxamide
—— 1-(1-(2,3-Dihydrobenzofuran-5-yl)propan-2-yl)-3-isopropylurea —— C15H22N2O2
1-(1-(2,3-Dihydrobenzofuran-5-yl)propan-2-yl)-3-isopropylurea
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(p-tolyl)methanesulfonamide —— C19H23NO3S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(p-tolyl)methanesulfonamide
—— 1-(3-chlorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)methanesulfonamide —— C18H20ClNO3S
1-(3-chlorophenyl)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)methanesulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-(4-fluorophenoxy)acetamide —— C19H20FNO3
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-(4-fluorophenoxy)acetamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-sulfonamide —— C20H23NO5S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-sulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(m-tolyl)methanesulfonamide —— C19H23NO3S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(m-tolyl)methanesulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)butane-1-sulfonamide —— C15H23NO3S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)butane-1-sulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-phenoxypropanamide —— C20H23NO3
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-phenoxypropanamide
—— 1-bromo-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)methanesulfonamide —— C12H16BrNO3S
1-bromo-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)methanesulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-4-propyl-1,2,3-thiadiazole-5-carboxamide —— C17H21N3O2S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-4-propyl-1,2,3-thiadiazole-5-carboxamide
—— 1-Cyclohexyl-3-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)urea —— C18H26N2O2
1-Cyclohexyl-3-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)urea
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-3,5-dimethylisoxazole-4-carboxamide —— C17H20N2O3
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-3,5-dimethylisoxazole-4-carboxamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-isopropyl-3,5-dimethyl-1H-pyrazole-4-sulfonamide —— C19H27N3O3S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-isopropyl-3,5-dimethyl-1H-pyrazole-4-sulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2,3-dihydrobenzofuran-5-sulfonamide —— C19H21NO4S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2,3-dihydrobenzofuran-5-sulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)propane-1-sulfonamide —— C14H21NO3S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)propane-1-sulfonamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(thiophen-2-yl)cyclopentanecarboxamide —— C21H25NO2S
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-1-(thiophen-2-yl)cyclopentanecarboxamide
—— 2-(4-chlorophenoxy)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)acetamide —— C19H20ClNO3
2-(4-chlorophenoxy)-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)acetamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-(p-tolyloxy)acetamide —— C20H23NO3
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-2-(p-tolyloxy)acetamide
—— 2-cyclopentyl-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)acetamide —— C18H25NO2
2-cyclopentyl-N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)acetamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-4-phenylbutanamide —— C21H25NO2
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-4-phenylbutanamide
—— N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-3-methoxy-1-methyl-1H-pyrazole-4-carboxamide —— C17H21N3O3
N-(1-(2,3-dihydrobenzofuran-5-yl)propan-2-yl)-3-methoxy-1-methyl-1H-pyrazole-4-carboxamide
—— N-[1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-yl]-3-thiophen-3-ylprop-2-enamide —— C18H19NO2S
N-[1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-yl]-3-thiophen-3-ylprop-2-enamide